Synthesis of geranylhydroquinone derivatives with potencial cytotoxic activity

Abstract

Recebido em 12/5/11; aceito em 29/8/11; publicado na web em 26/9/11 Natural geranylhydroquinone 1 and geranyl-p-methoxyphenol 2 were prepared by Electrophilic Aromatic Substitution (EAS) reactions between geraniol and 1,4-hydroquinone or p-methoxyphenol respectively, using BF 3 •Et 2 O as a catalyst. Furthermore, natural geranylquinone 3, geranyl-1,4-dimethoxyquinone 4 and the new geranyl-4-methoxyphenyl acetate 5 were obtained by chemical transformations of 1 and 2. The compounds were evaluated for their in vitro cytotoxicity activities against cultured human cancer cells of PC-3 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma, and Dermal Human Fibroblasts DHF. IC 50 values were in the µM range.

Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives

“…The direct coupling between geraniol and commercially available 4-methoxyphenol using acetonitrile/AgNO 3 gives compound 6 as a unique product with 18% yield, which is almost twice the yield reported for the same reaction in dioxane (10%) [ 15 ]. However, this yield is much lower than that reported for the reaction of 4-methoxyphenol with geranyl bromide in the presence of NaH, which leads to 6 with a 56% yield [ 16 ].…”

Synthesis and NMR Structure Determination of New Linear Geranylphenols by Direct Geranylation of Activated Phenols

“…Our first objective was the preparation of compounds 2, 4-5, using the coupling method previously described by us [18,19] with geraniol and commercially available hydroquinone and orcinol, respectively. In this case, 2-geranylhydroquinone 2 was obtained with 28 % yield, whereas the compounds 4 and 5 were obtained with 12.6 % and 27.6 % yields, respectively.…”

“…The synthesis of compound 13 (geranylphloroglucinol proposed name by us in analogy with the name of geranylorcinol) was development by direct geranylation reactions between phloroglucinol (benzene-1,3,5-triol) and geraniol with a 4,2 % yield. Later, the compound 13 was methylated with dimethylsulfate in acetone as was previously described by us for other compounds [18]. The trimethoxylated derivative 14 was obtained with a 98.5 % yield.These reactions are shown in scheme 1.…”

“…[18] [19]. On another hand, several factors highlight the urgent need for the development of new strategies for the control of phytopathogen fungus Botrytis cinerea and other plagues affecting important Chilean agricultural crops.…”

Cytotoxic Effect of Geranylphenol Derivatives in the Human Breast Cancer Cell Line MDA-MB-231 and Gastric Cancer Cell Line MKN74

“…activity was found for 2-geranylbenzoquinone and 2-geranylhydroquinone, and some synthetic geranylphenol-geranylmethoxy derivatives were also described as cytotoxic [27][28][29][30][31] . Another interesting study reported the anticancer activity and probable mechanism of action of 3-demetylubiquinone Q2 32 .…”